Diisopropylethylamine → HCID 89466041, compound

HRID 1184584Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[C@H:13]3[CH2:14][NH:15][CH2:16][CH2:17][N:12]3[CH2:11][CH2:10]2)=[N:6][CH:7]=1.F[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[C@H:13]3[CH2:14][N:15]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=4)[CH2:16][CH2:17][N:12]3[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of Example 101B (53 mg, 0.21 mmol) and 2-fluoro-6-(trifluoromethyl)pyridine (41 mg, 0.25 mmol) in dimethyl sulfoxide (0.7 mL) was added N,N-diisopropylethylamine (0.3 mL, 1.73 mmol). The mixture was heated to 90° C. and stirred for 16 hours and then concentrated. The residue was purified via HPLC (Gilson®, Xbridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=248 nm) to give the title compound. 1H NMR (300 MHz, methanol-d4) δ ppm 1.81-1.96 (m, 1 H), 2.13-2.31 (m, 3 H), 2.40-2.53 (m, 1 H), 2.94-3.05 (m, 2 H), 3.16-3.25 (m, 2 H), 4.34-4.43 (m, 1 H), 4.50 (dd, 1H, J=12, 3 Hz), 5.59 (ddd, 1H, J=7, 4, 2 Hz), 6.81 (d, 1H, J=8 Hz), 6.96 (dd, 2H, J=8, 5 Hz), 7.61-7.71 (m, 2 H), 8.12 (d, 1H, J=2 Hz); MS (DCI) m/z 399 (M+H)+.

Workup

concentrationconcentrated
customThe residue was purified via HPLC (Gilson®, Xbridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=248 nm)

Sources & evidence

ORD record: ord-f31c66602de44cf3a7a37fb968b7d8e4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669255B2

Reaction notes

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